While sipping our caffeinated beverages each morning, we’re also likely to be shaking our heads at news reports of public figures trying to recover from PR nightmares brought on by bad timing:

• With his re-election already in doubt, soon-to-be-ex British Prime Minister Gordon Brown is mortified to be caught open-mic’d ranting about being annoyed by Jane Q. Voter.

• The Virginia Department of Transportation announces 678 layoffs the same morning a huge snowstorm blankets the state’s roadways, overwhelming snow-plowing crews already short-staffed by previous layoffs.

• Reality star Kim Kardashian apologizes profusely for publicizing her new “pet” chimp—actually rented to punk her mom—just three days after another pet chimp makes worldwide headlines for viciously attacking a Connecticut woman.

Although few of our blunders will make news, we still want to avoid sabotaging our plans by setting them in motion at awkward moments—especially if we’re planning to negotiate better circumstances at work. Some advice:

• Explore your motives. Why this? Why now? If your response is that this is available now … wrong answer. When you’re out of work and desperate, you do what you have to do. But when you’re employed, you shouldn’t leap at every new opportunity with the predictability of a hurdler running the course. That doesn’t tell decision-makers you have a plan and want to take the logical next step; it tells them you’ll take anything that gets you out of your current position or promises a few extra bucks. Before putting yourself on the line, be sure this is what you really want and not just an attempt to outrace the other rats.

• Explore your surroundings. It’s been a while since you’ve had a cost-of-living increase, so you decide to approach your supervisor about a raise. Whoa! Don’t assume that because you haven’t received a recent increase—or you’ve heard another employee has—it’s a good time to press for more money. First, research the financial health of your industry, your community, and your organization. Don’t put yourself in the awkward position of asking for something your boss can’t give. And try not to focus on what’s happening with other departments or workers. Often companies compensate different departments, those assigned to different projects, or people at different pay grades from different revenue streams. At various times, some funding sources are healthier than others. You may be trying to pick an empty pocket.

• Explore your value.  It doesn’t matter that you’ve brought in 30 clients and generated $10 million in revenue since you’ve been with your employer, if your recent output has been subpar. It doesn’t even matter that you’ve outperformed half the staff, if you’ve underperformed your own track record. You’ve taught your bosses what to expect from you. And if you’ve failed to perform to that standard, this is not the time to ask for extra money or a plum assignment. Instead of thinking what the company can do for you, think about how you can enhance your worth to the organization.

Postponing your request doesn’t mean giving up on your plans. But waiting for a better time may mean the difference between success and an embarrassing failure.